Baseninduzierte umlagerungen von 3,9 dioxatricyclo[3.3.1.02,4]nonan-7-onen zu m-hydroxyphenylcarbonyl-verbindungen |
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Authors: | Baldur Föhlisch Otto Herrscher |
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Affiliation: | Institut für Organische Chemie, Biochemie und Isotopenforschung der Universitát Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, BundesrepublikDeutschland |
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Abstract: | 8-Oxabicyclo[3.2.1]oct-6-en-3-ones (5), easily available by [4+3]cycloaddition, were epoxidised at the CC double bond. The 3,9-dioxatricyclo[3.3.1.02,4]nonan-7-ones (6) thus obtained are rearranged on treatment with sodium ethoxide in ethanol to form 3-hydroxybenzaldehydes (8a-d) and 3-hydroxy-2,4,5-trimethylacetophenone (8e) in good yields. As intermediates of these rearrangements, 8-hydroxy-6-oxatricyclo [3.2.1.02,7]octan-3-ones are postulated ; the trimethyl derivative 7g and the 6-carba-derivatives 4a,b could be isolated. |
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